diff --git a/packages/specs/schema/src/decorators/common/nullable.spec.ts b/packages/specs/schema/src/decorators/common/nullable.spec.ts
index 11a25ad13e7..23506f760be 100644
--- a/packages/specs/schema/src/decorators/common/nullable.spec.ts
+++ b/packages/specs/schema/src/decorators/common/nullable.spec.ts
@@ -1,4 +1,4 @@
-import {Nullable, Property, Required} from "@tsed/schema";
+import {Nullable, Property, Required, SpecTypes} from "@tsed/schema";
 import {expect} from "chai";
 import {getJsonSchema} from "../../utils/getJsonSchema";
 
@@ -151,4 +151,69 @@ describe("@Nullable", () => {
       type: "object"
     });
   });
+  it("should declare any prop (many Models + Nullable)", () => {
+    // WHEN
+    class Nested1 {
+      @Property()
+      id: string;
+
+      @Property()
+      top: string;
+    }
+
+    class Nested2 {
+      @Property()
+      id: string;
+
+      @Property()
+      other: string;
+    }
+
+    class Model {
+      @Nullable(Nested1, Nested2)
+      prop2: Nested1 | Nested2 | null;
+    }
+
+    // THEN
+    expect(getJsonSchema(Model, {specType: SpecTypes.OPENAPI})).to.deep.equal({
+      definitions: {
+        Nested1: {
+          properties: {
+            id: {
+              type: "string"
+            },
+            top: {
+              type: "string"
+            }
+          },
+          type: "object"
+        },
+        Nested2: {
+          properties: {
+            id: {
+              type: "string"
+            },
+            other: {
+              type: "string"
+            }
+          },
+          type: "object"
+        }
+      },
+      properties: {
+        prop2: {
+          anyOf: [
+            {
+              $ref: "#/components/schemas/Nested1"
+            },
+            {
+              $ref: "#/components/schemas/Nested2"
+            }
+          ],
+          nullable: true
+        }
+      },
+      type: "object"
+    });
+  });
 });
diff --git a/packages/specs/schema/src/domain/JsonSchema.ts b/packages/specs/schema/src/domain/JsonSchema.ts
index bbd9b890b96..68f59c675ca 100644
--- a/packages/specs/schema/src/domain/JsonSchema.ts
+++ b/packages/specs/schema/src/domain/JsonSchema.ts
@@ -731,13 +731,28 @@ export class JsonSchema extends Map<string, any> implements NestedGenerics {
   }
 
   any(...types: any[]) {
-    types = uniq(types.length ? types : ["integer", "number", "string", "boolean", "array", "object", "null"]).map(getJsonType);
+    const hasClasses = types.filter((type) => isClass(type));
+
+    if (hasClasses.length >= 2) {
+      this.anyOf(
+        types.filter((value) => {
+          if (value !== null) {
+            this.nullable = true;
+            return false;
+          }
+          return true;
+        })
+      );
+    } else {
+      // TODO when OS3 will the only minimal supported version, we'll can remove this code
+      types = uniq(types.length ? types : ["integer", "number", "string", "boolean", "array", "object", "null"]).map(getJsonType);
 
-    if (types.includes("null")) {
-      this.nullable = true;
-    }
+      if (types.includes("null")) {
+        this.nullable = true;
+      }
 
-    this.type(types.length === 1 ? types[0] : types);
+      this.type(types.length === 1 ? types[0] : types);
+    }
 
     return this;
   }